IMIQUIMOD

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Search structure


Trade Names	ALDARA IMIQUIMOD ZYCLARA
Synonyms	Aldara Imiquimod NSC-369100 NSC-759651 R-837 S-26308 S26308 Zyclara
Status
Molecule Category	UNKNOWN
ATC	D06BB10
UNII	P1QW714R7M
EPA CompTox	DTXSID7041047


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	DOUYETYNHWVLEO-UHFFFAOYSA-N
Smiles	CC(C)Cn1cnc2c(N)nc3ccccc3c21
InChI	InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C14H16N4
Molecular Weight	240.31
AlogP	2.82
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	2.0
Polar Surface Area	56.73
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	18.0

Bioactivity

Mechanism of Action	Action	Reference
Toll-like receptor 7 agonist	AGONIST	FDA PubMed


Protein: Toll-like receptor 7 Description: Toll-like receptor 7 Organism : Homo sapiens Q9NYK1 ENSG00000196664

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	646	-	-	-
Membrane receptor Toll-like and Il-1 receptors	2120-12100	-	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	19.72 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-4.31 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.02 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.02 %
Inhibition of MTH1 (unknown origin) using 8-oxo-dGTP as substrate preincubated for 15 mins followed by substrate addition and measured after 20 mins by PPiLight detection reagent based luminescence assay	Homo sapiens	646.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	36704
ChEMBL	CHEMBL1282
DrugBank	DB00724
DrugCentral	1429
FDA SRS	P1QW714R7M
Human Metabolome Database	HMDB0014862
Guide to Pharmacology	5003
KEGG	D02500
PDB	6T0
PharmGKB	PA449972
PubChem	57469
SureChEMBL	SCHEMBL26136
ZINC	ZINC000019632912

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).